Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under ­experimental sonogashira conditions

Mikkel Andreas Christensen; Morten Rimmen Pedersen; Mogens Brøndsted Nielsen

doi:10.1055/s-0033-1339891

Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions

Mikkel Andreas Christensen, Morten Rimmen Pedersen, Mogens Brøndsted Nielsen

Kemisk Institut

6 Citationer (Scopus)

Abstract

The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

Originalsprog	Engelsk
Tidsskrift	SYNLETT: Accounts and Rapid Communications in Chemical Synthesis
Vol/bind	24
Udgave nummer	20
Sider (fra-til)	2715-2719
Antal sider	5
ISSN	0936-5214
DOI	https://doi.org/10.1055/s-0033-1339891
Status	Udgivet - 17 dec. 2013

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10.1055/s-0033-1339891

Citationsformater

Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions. / Christensen, Mikkel Andreas; Pedersen, Morten Rimmen; Nielsen, Mogens Brøndsted.

I: SYNLETT: Accounts and Rapid Communications in Chemical Synthesis, Bind 24, Nr. 20, 17.12.2013, s. 2715-2719.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

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AU - Christensen, Mikkel Andreas

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N2 - The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

AB - The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

U2 - 10.1055/s-0033-1339891

DO - 10.1055/s-0033-1339891

M3 - Journal article

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JO - Synlett

JF - Synlett

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ER -

Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under ­experimental sonogashira conditions

Abstract

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Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions